EP0005145B1 - Verfahren zur Herstellung von 5-(2-Bromäthyliden)-2(3H)-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalin-2-on und 5-Äthenyl-2(3H)-4a-methyl-4,4a,7,8-tetrahydronaphthalin-2-on daraus durch Dehydrobromierung - Google Patents

Verfahren zur Herstellung von 5-(2-Bromäthyliden)-2(3H)-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalin-2-on und 5-Äthenyl-2(3H)-4a-methyl-4,4a,7,8-tetrahydronaphthalin-2-on daraus durch Dehydrobromierung Download PDF

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Publication number
EP0005145B1
EP0005145B1 EP79100460A EP79100460A EP0005145B1 EP 0005145 B1 EP0005145 B1 EP 0005145B1 EP 79100460 A EP79100460 A EP 79100460A EP 79100460 A EP79100460 A EP 79100460A EP 0005145 B1 EP0005145 B1 EP 0005145B1
Authority
EP
European Patent Office
Prior art keywords
methyl
ethenyl
bromoethylidene
lithium
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP79100460A
Other languages
English (en)
French (fr)
Other versions
EP0005145A1 (de
Inventor
Malcolm Rice Bell
John Lawrence Herrmann, Jr.
Vahan Akullian
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
STWB Inc
Original Assignee
Sterling Drug Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of EP0005145A1 publication Critical patent/EP0005145A1/de
Application granted granted Critical
Publication of EP0005145B1 publication Critical patent/EP0005145B1/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
    • C07C49/653—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration

Definitions

  • pyridine in the foregoing example can be replaced by 4-methylpyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine or 4-ethyl-2-methylpyridine with similar results.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

1. Verfahren zum Erzeugen von 5-Äthenyl-2(3H)-4a-methyl-4,4a,7,8-tetrahydronaphthalin-2-on aus 5-(2-Bromäthyliden-2(3H)-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalin-2-on, dadurch gekennzeichnet, daß die genannte Verbindung in einem inerten Lösungsmittel mit mindestens einem Dehydrohalogeniermittel dehydrohalogeniert wird, das Pyridin, ein niederalkyliertes Pyridin, ein Alkalimetallphenoxid, ein nieder-alkyliertes Alkalimetallphenoxid, Lithiumchlorid, Lithiumbromid oder Lithiumcarbonat ist.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß das Dehydrohalogeniermittel ein Gemisch von Lithiumbromid und Lithiumcarbonat ist.
3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß das inerte Lösungsmittel Dimethylformamid ist.
4. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, daß das 5-(2-Bromäthyliden-2(3H)-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalin-2-on in situ durch Umsetzen von 5-Äthenyl-4,4a,5,6,7,8-hexahydronaphthalin-2-on mit Phosphortribromid erzeugt wird.
EP79100460A 1978-03-13 1979-02-16 Verfahren zur Herstellung von 5-(2-Bromäthyliden)-2(3H)-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalin-2-on und 5-Äthenyl-2(3H)-4a-methyl-4,4a,7,8-tetrahydronaphthalin-2-on daraus durch Dehydrobromierung Expired EP0005145B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US885776 1978-03-13
US05/885,776 US4157349A (en) 1978-03-13 1978-03-13 Dehydrohalogenation process

Publications (2)

Publication Number Publication Date
EP0005145A1 EP0005145A1 (de) 1979-11-14
EP0005145B1 true EP0005145B1 (de) 1981-12-30

Family

ID=25387672

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79100460A Expired EP0005145B1 (de) 1978-03-13 1979-02-16 Verfahren zur Herstellung von 5-(2-Bromäthyliden)-2(3H)-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalin-2-on und 5-Äthenyl-2(3H)-4a-methyl-4,4a,7,8-tetrahydronaphthalin-2-on daraus durch Dehydrobromierung

Country Status (7)

Country Link
US (1) US4157349A (de)
EP (1) EP0005145B1 (de)
JP (1) JPS54128559A (de)
CA (1) CA1099743A (de)
DE (1) DE2961635D1 (de)
DK (1) DK94579A (de)
IE (1) IE48256B1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4680142A (en) * 1982-03-02 1987-07-14 International Flavors & Fragrances Inc. Process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone, intermediates used in said process and novel crystalline form of same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3086027A (en) * 1960-01-22 1963-04-16 Lilly Co Eli 19-nor-4, 9(10)-steroids and process
US3920748A (en) * 1972-06-12 1975-11-18 Hoffmann La Roche Steroid total synthesis and intermediates
US3920749A (en) * 1973-08-17 1975-11-18 Hoffmann La Roche Process for dehydrating vinyl-substituted tertiary alcohols

Also Published As

Publication number Publication date
EP0005145A1 (de) 1979-11-14
DE2961635D1 (en) 1982-02-18
DK94579A (da) 1979-09-14
US4157349A (en) 1979-06-05
IE48256B1 (en) 1984-11-14
IE790265L (en) 1979-09-13
JPS54128559A (en) 1979-10-05
CA1099743A (en) 1981-04-21

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